Earlier this year, Michael Bloomberg, the Republican mayor turned centrist thought leader, announced that he would pour $80 million of his formidable net worth into flipping the House for Democrats in the midterms—the biggest pledge made by any single donor so far this cycle. (Sheldon Adelson, Bloomberg’s counterpart on the right, donated a paltry $30 million.) Bloomberg may have appeared to be transitioning to a kingmaker, but it quickly became clear that his act of generosity masked ulterior motives, as eight-figure political donations typically do. Bloomberg, sources told the New York Post, was eyeing the throne, himself. On Thursday, The Times of Londonconfirmed that the finance titan has been telling confidants he is gearing up for the Democratic primary, believing Donald Trump has cleared the way for a (more successful) businessman to be president. “Mike Bloomberg told me he is going to run in 2020,” a source told the British paper. “He has the money to see it through while other candidates knock themselves out.”

The 76-year-old refrained from running in 2016 as an Independent, concerned that a three-way race could land Trump in the White House. But Bloomberg’s calculus has since changed. With his growing influence in the Democratic Party, Bloomberg could conceivably gain traction in a crowded race where, Joe Biden aside, many prospective candidates lack a broadly appealing political brand. Last month, Trump’s former campaign manager, Corey Lewandowski,pointed out all the ways in which Bloomberg could give Trump a “run for his money”: he’s created “tens of thousands of jobs over the course of his lifetime,” he’s a self-made billionaire (about $52 billion, to be precise), and he has a positive record of running the nation’s biggest city. “That is a story the American people like and he’s an outsider,” Lewandowski acknowledged. “I think it would be a very competitive race.”

Lewandowski’s endorsement is somewhat self-serving: Bloomberg, as he well knows, is easily characterized as the sort of out-of-touch technocrat that Republicans love to hate. (Look no further than the uproar over Bloomberg’s ill-fated push to ban soda in New York City.) And, as Jeb Bushlearned the hard way, a massive campaign war chest doesn’t necessarily translate into votes. Trump’s triumph over the Republican field came not as a result of big spending, but from a potent combination of his political outsider status, a record-breaking $2 billion in earned media, and an intensely loyal grassroots following; his status as a wealthy businessman was arguably a secondary factor. Several Democratic primaries seem to carry a similar message: Alexandria Ocasio-Cortez and her $300,709 war chest handily defeatedJoe Crowley’s $1.5 million spending blitz. In the Florida governor’s race, progressive Andrew Gillum often mentioned that he was the only non-millionaire in the race; he ultimately spent just $6.5 million to win the Democratic primary, compared to his rivals, who each dropped tens of millions. Both candidates relied heavily on online messaging and boasted strong grassroots support.

While Bloomberg can claim that he’s a better, even-keeled, more-qualified version of Trump, he’s certainly not a political outsider, nor is he a grassroots hero. He has no natural constituency, besides charter-school Democrats, the set of Morning Joe, and fellow members of the donor class. His stubborn brand of plutocratic centrism, as well as his overzealous use of stop-and-frisk tactics, would likely be a nonstarter for progressives, as well as the blue-collar workers who flipped to Trump in 2016. If Bloomberg does decide to run, he would enter a party riven by identity crises stemming from the fierce primary between Hillary Clinton and Bernie Sanders, and most recently evident in the race for New York governor between Democratic Socialist Cynthia Nixon and Albany swamp king Andrew Cuomo. While Nixon ran on a platform for change, Cuomo successfully fended her off by touting his progressive experience and political skill, but not before adopting many of her further-afield stances, such as restoring voting rights to parolees and reversing his stance on legalizing marijuana. If Cuomo, a staunchly progressive governor in his own right, was forced to tack further to the left in order to win, one cannot imagine how Bloomberg, with his appeals to the party’s “radical center,” could score a primary victory.

While Cuomo’s win could be interpreted as a sign that Democratic voters are stodgier than Twitter would suggest, it’s also true that Cuomo’s control over party machinery gave him a major edge over Nixon. It’s tempting for Bloomberg and other billionaire centrist hopefuls—Howard Schultz, Mark Cuban, perhaps Bob Iger—to follow Trump’s lead. But their money will only propel them so far, especially should they come up against a certain charismatic ex-Scrantonite.